CN106573938B - Compound for organic electronic element, and organic electronic element and electronic device using same - Google Patents

Compound for organic electronic element, and organic electronic element and electronic device using same Download PDF

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CN106573938B
CN106573938B CN201580028337.6A CN201580028337A CN106573938B CN 106573938 B CN106573938 B CN 106573938B CN 201580028337 A CN201580028337 A CN 201580028337A CN 106573938 B CN106573938 B CN 106573938B
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organic electronic
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CN106573938A (en
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朴钟光
严佳永
朴亨根
曺惠敏
李大元
朴正焕
崔莲姬
吕承垣
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DukSan Neolux Co Ltd
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Abstract

The present invention provides a compound capable of improving luminous efficiency, reducing driving voltage, and increasing the lifetime of an element, and an organic electronic element and an electronic device using the same.

Description

Compound for organic electronic element, and organic electronic element and electronic device using same
Technical Field
The present invention relates to a compound for an organic electronic element, an organic electronic element using the compound, and an electronic device.
Background
In general, the organic light emitting phenomenon refers to a phenomenon of converting electric energy into light energy of an organic material using the organic material. An organic electronic element utilizing an organic light emitting phenomenon generally has a structure including an anode, a cathode, and an organic material layer interposed therebetween. In many cases, the organic material layer may have a multilayer structure including a plurality of layers made of different materials in order to improve efficiency and stability of the organic electronic element, and may include, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like.
Materials used as the organic material layer in the organic electronic element may be classified into light emitting materials and charge transport materials, such as hole injection materials, hole transport materials, electron injection materials, and the like, according to their functions. Further, light emitting materials can be classified into a high molecular weight type and a low molecular weight type according to their molecular weights, and can also be classified into a fluorescent material derived from an electron excited singlet state and a phosphorescent material derived from an electron excited triplet state according to their light emitting mechanisms. In addition, the light emitting materials may be classified into blue, green and red light emitting materials according to their light emitting colors, and yellow and orange light emitting materials required for better natural color reproduction.
Currently, as the size of displays in the portable display market becomes larger and larger, more and more power consumption is required. Therefore, in portable displays with limited battery power, power consumption is a very important factor and efficiency and lifetime issues are also addressed.
Efficiency, lifetime, driving voltage, etc. are related to each other. For example, if the efficiency is increased, the driving voltage is relatively decreased, and as the driving voltage is decreased, crystallization of the organic material due to joule heat generated during operation is decreased, with the result that the lifetime shows an increased tendency. However, efficiency cannot be maximized by simply improving the organic material layer. This is because both long life and high efficiency can be achieved when an optimum combination of the energy level and T1 value between layers included in the organic material layer, intrinsic material properties (mobility, interface properties, etc.), and the like is given.
Generally, electrons transported from the electron transport layer to the light emitting layer and holes transported from the hole transport layer to the light emitting layer recombine to form excitons.
However, holes move faster than electrons, and excitons formed in the light-emitting layer move to the electron transport layer, resulting in charge imbalance in the light-emitting layer, resulting in light emission in the electron transport layer interface.
When light emission occurs in the interface of the hole transport layer, the organic electroluminescent device has a disadvantage of lowering color purity and efficiency. In particular, in the manufacture of organic electronic components, high temperature stability is deteriorated, resulting in short life span of the organic electronic components. Therefore, there is a need to develop an electron transport material (adv. funct. mater.2013,23,1300023) having improved hole blocking capability while having high temperature stability and high electron mobility (within the driving voltage range of a blue element of an electron mobility all device (full device)).
When only one material is used as a light emitting material, a problem of a shift of the maximum light emitting wavelength to a longer wavelength due to an intermolecular interaction, and a problem of a decrease in efficiency of the corresponding element due to deterioration of color purity, or a decrease in light emitting efficiency occur. For this reason, a host/dopant system may be used as a light emitting material in order to improve color purity and improve luminous efficiency through energy transfer. This is based on the following principle: if a small amount of dopant having a smaller energy band gap than the host forming the light emitting layer is mixed in the light emitting layer, excitons generated in the light emitting layer are transferred to the dopant, and thus the light emitting efficiency is high. In this regard, since the wavelength of the host is shifted to the wavelength band of the dopant, light having a desired wavelength may be obtained according to the type of the dopant.
However, the efficiency cannot be maximized by merely introducing the host/dopant, and the maximum efficiency can be obtained by characteristics exhibited from a combination of a core and a sub-substituent(s) of the light emitting material and an optimal combination of the host/dopant.
That is, in order for an organic electronic device to sufficiently exhibit excellent characteristics, it is most important that materials constituting an organic material layer in the device, for example, a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, and the like, be supported by stable and effective materials, but development of stable and effective materials for an organic material layer of an organic electronic device has not been sufficiently achieved. Therefore, there is a continuous need for the development of new materials, and particularly, there is an urgent need for the development of electron transport materials and light emitting materials.
Disclosure of Invention
Technical problem
In order to solve the above-mentioned problems occurring in the prior art, it is an object of the present invention to provide a compound capable of achieving high luminous efficiency, low driving voltage and improved element life, an organic electronic element using the same, and an electronic device.
Technical scheme
According to one aspect of the present invention, there is provided a compound represented by the following formula.
Figure BDA0001164304760000031
In another aspect of the present invention, there are provided an organic electronic element using the compound represented by the above formula, and an electronic device.
Advantageous effects
The use of the compound according to the present invention can achieve high luminous efficiency and low driving voltage of the element, and significantly improve the improved lifetime of the element.
Drawings
Fig. 1 shows an embodiment of an organic electroluminescent element according to the present invention.
Detailed Description
Hereinafter, some embodiments of the present invention will be described in detail with reference to the accompanying illustrative drawings.
In the designation of reference numerals for components in the respective drawings, it should be noted that the same elements will be denoted by the same reference numerals although shown in different drawings. Further, in the following description of the present invention, a detailed description of known functions and configurations incorporated herein will be omitted when it may make the subject matter of the present invention rather unclear.
In addition, in describing the components of the present invention, terms such as first, second, A, B, (a), (b), etc. may be used herein. Each of these terms is not used to define the nature, order, or sequence of the corresponding components, but is used merely to distinguish the corresponding component from other components. It should be noted that if one component is described in the specification as being "connected," "coupled," or "joined" to another component, a third component may be "connected," "coupled," and "joined" between the first and second components, although the first component may be directly connected, coupled, or joined to the second component.
As used in the specification and appended claims, the following are the meanings of the terms, unless otherwise indicated.
The term "halo" or "halogen" as used herein, unless otherwise indicated, includes fluorine (F), bromine (Br), chlorine (Cl) and iodine (I).
As used herein, unless otherwise indicated, the term "alkyl" or "alkyl group" has a single bond of 1 to 60 carbon atoms and refers to an aliphatic functional group that includes a linear alkyl group, a branched chain alkyl group, a cycloalkyl group (alicyclic), or an alkyl group substituted with a cycloalkyl group.
The term "haloalkyl" or "haloalkyl" as used herein, unless otherwise specified, refers to an alkyl group substituted with a halogen.
The term "heteroalkyl," as used herein, refers to an alkyl group in which at least one carbon atom is replaced with a heteroatom.
The term "alkenyl" or "alkynyl" as used herein, unless otherwise specified, has, but is not limited to, a double or triple bond of 2 to 60 carbon atoms and includes linear alkyl or branched alkanyl.
The term "cycloalkyl" as used herein, unless otherwise specified, refers to an alkyl group forming a ring having 3 to 60 carbon atoms, but is not limited thereto.
The terms "alkoxy group," "alkoxy" or "alkyloxy" as used herein refer to an alkyl group attached to an oxygen radical, but are not limited to, and unless otherwise specified, have from 1 to 60 carbon atoms.
The term "alkenyloxy group", "alkenyloxy group" or "alkenyloxy" as used herein refers to an alkenyl group attached to an oxygen radical, but is not limited to, and unless otherwise specified, has from 2 to 60 carbon atoms.
The term "aryloxy group" or "aryloxy group" as used herein refers to an aryl group attached to an oxygen radical, but is not limited to, and has 6 to 60 carbon atoms.
Unless otherwise specified, the terms "aryl" and "arylene" each have 6 to 60 carbon atoms, but are not limited thereto. Aryl or arylene herein refers to monocyclic or polycyclic aromatic groups and includes aromatic rings formed in combination with adjacent substituents attached thereto or involved in a reaction. Embodiments of aryl groups may include phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, fluorenyl, spirofluorenyl, and spirobifluorenyl groups.
The prefix "aryl" or "aryl (ar)" refers to a group substituted with an aryl group. For example, arylalkyl can be an alkyl substituted with aryl, arylalkenyl can be an alkenyl substituted with aryl, and the group substituted with aryl has the number of carbon atoms as defined herein.
Further, when the prefix is named subsequently, it indicates that the substituents are listed in the order described first. For example, arylalkoxy refers to alkoxy substituted with aryl, alkoxycarbonyl refers to carbonyl substituted with alkoxy, and arylcarbonylalkenyl also refers to alkenyl substituted with arylcarbonyl, where arylcarbonyl can be carbonyl substituted with aryl.
The term "heteroalkyl," as used herein, unless otherwise specified, refers to an alkyl group containing one or more heteroatoms. The term "heteroaryl" or "heteroarylene" as used herein, unless otherwise specified, refers to, but is not limited to, an aryl or arylene group having 2 to 60 carbon atoms and containing one or more heteroatoms, including at least one of monocyclic and polycyclic, and may also be formed in combination with an adjacent group.
The term "heterocyclyl" as used herein, unless otherwise specified, contains one or more heteroatoms, has 2 to 60 carbon atoms, includes at least one of homocyclic and heterocyclic rings, and may also be formed in combination with adjacent groups.
The term "heteroatom" as used herein means N, O, S, P or Si unless otherwise specified.
In addition, "heterocyclic" may also include compounds containing SO2The ring of the carbon forming the ring is substituted. For example, "heterocyclyl" includes the following compounds.
Figure BDA0001164304760000051
As used herein, unless otherwise specified, the term "aliphatic" refers to aliphatic hydrocarbons having from 1 to 60 carbon atoms, and the term "alicyclic" refers to aliphatic hydrocarbon rings having from 3 to 60 carbon atoms.
Unless otherwise specified, the term "ring" refers to an aliphatic ring having 3 to 60 carbon atoms, an aromatic ring having 6 to 60 carbon atoms, a heterocyclic ring having 2 to 60 carbon atoms, or a fused ring formed by a combination thereof, and includes saturated or unsaturated rings.
Heterocompounds or heterogroups other than the above heterocompounds each contain, but are not limited to, one or more heteroatoms.
The term "carbonyl" as used herein, unless otherwise indicated, is represented by — COR ', where R' may be hydrogen, alkyl having 1 to 20 carbon atoms, aryl having 6 to 30 carbon atoms, cycloalkyl having 3 to 30 carbon atoms, alkenyl having 2 to 20 carbon atoms, alkynyl having 2 to 20 carbon atoms, or a combination thereof.
The term "ether" as used herein, unless otherwise indicated, is represented by-R-O-R ', wherein R' can be hydrogen, alkyl having 1 to 20 carbon atoms, aryl having 6 to 30 carbon atoms, cycloalkyl having 3 to 30 carbon atoms, alkenyl having 2 to 20 carbon atoms, alkynyl having 2 to 20 carbon atoms, or combinations thereof.
As used herein, unless otherwise indicated, the term "substituted or unsubstituted" means that the substitution is by at least one substituent selected from the group consisting of, but not limited to, deuterium, halogen, amino, nitrile, nitro, C1-C20Alkyl radical, C1-C20Alkoxy radical, C1-C20Alkylamino radical, C1-C20Alkylthio (alkylthio), C6-C20Arylthio (arylthio), C2-C20Alkenyl radical, C2-C20Alkynyl, C3-C20Cycloalkyl radical, C6-C60Aryl, C substituted by deuterium6-C20Aryl radical, C8-C20Arylalkenyl, silyl, boryl, germyl and C5-C20A heterocyclic group.
Unless otherwise specified, the formula used in the present invention is defined as an index definition (indexdefination) of a substituent of the following formula.
Figure BDA0001164304760000061
Wherein, when a is an integer of 0, the substituent R1Absent, when a is the integer 1, the only R1To any one of the carbon atoms constituting the phenyl ring, when a is an integer of 2 or 3, the substituent R1May be the same or different and are attached to a benzene ring as follows. When a is an integer of 4 to 6, the substituent R1May be the same or different, and is linked to a benzene ring in a similar manner to when a is an integer of 2 or 3,the hydrogen atom of the carbon component attached to the benzene ring is not represented as usual.
Figure BDA0001164304760000062
Fig. 1 shows an organic electronic component according to an embodiment of the present invention.
Referring to fig. 1, an organic electronic component 100 according to an embodiment of the present invention includes a first electrode 120, a second electrode 180, and an organic material layer containing the compound of the present invention between the first electrode 120 and the second electrode 180, formed on a substrate 110. Here, the first electrode 120 may be an anode (positive electrode), and the second electrode 180 may be a cathode (negative electrode). In the case of an inverted organic electronic component, the first electrode may be a cathode and the second electrode may be an anode.
The organic material layer includes a hole injection layer 130, a hole transport layer 140, an emission layer 150, an electron transport layer 160, and an electron injection layer 170, which are sequentially formed on the first electrode 120. Here, a layer included in the organic material layer may not be formed except the light emitting layer 150. The organic material layer may further include a hole blocking layer, an electron blocking layer, an emission auxiliary layer 151, a buffer layer 141, etc., and the electron transport layer 160, etc., may serve as the hole blocking layer.
Although not shown, the organic electronic element according to an embodiment of the present invention may further include at least one protective layer or one capping layer formed on at least one side of the first and second electrodes, the side being the side opposite to the organic material layer.
The compound of the present invention used in the organic material layer may be used as a host material, a dopant material, or a capping layer material in the hole injection layer 130, the hole transport layer 140, the electron transport layer 160, the electron injection layer 170, or the light emitting layer 150. For example, the compound of the present invention may be used as the light emitting layer 150, the hole transport layer 140, and/or the emission auxiliary layer 151.
Since a band gap, an electrical property, an interface property, and the like may vary even in the same core depending on the type and position of a substituent to be attached, it is very important what the type of core and the combination of substituents attached to the core are. In particular, when an optimum combination of the energy level and the value of T1, intrinsic material properties (mobility, interface properties, etc.), and the like between the respective layers included in the organic material layer is given, both long life and high efficiency can be achieved.
Therefore, in the present invention, the combination of the energy level and the T1 value between layers, the intrinsic material properties (mobility, interface properties, etc.), and the like included in the organic material layer is optimized by forming the light-emitting layer or the emission auxiliary layer using the compound represented by formula I, so that the lifetime and efficiency of the organic electronic element can be simultaneously improved.
An organic electronic component according to an embodiment of the present invention can be manufactured using a PVD (physical vapor deposition) method. For example, the organic electronic element may be manufactured by depositing a metal, a conductive metal oxide, or a mixture thereof on a substrate to form the anode 120, forming organic material layers including the hole injection layer 130, the hole transport layer 140, the light emitting layer 150, the electron transport layer 160, and the electron injection layer 170 thereon, and then depositing a material that can be used as the cathode 180 thereon.
Further, the organic material layer may be manufactured in such a manner that a small number of layers are formed using various polymer materials through a soluble process or a solvent process, such as spin coating, dip coating, blade coating, screen printing, inkjet printing, or thermal transfer, instead of deposition. Since the organic material layer according to the present invention may be formed in various ways, the scope of the present invention is not limited by the method of forming the organic material layer.
The organic electronic element according to an embodiment of the present invention may be a top emission type, a bottom emission type, or a dual emission type, depending on the material used.
WOLED (white organic light emitting device) easily allows formation of ultra-high definition images, and has excellent workability as well as enjoying advantages of fabrication using conventional color filter technology for LCDs. In this regard, various structures of WOLEDs used as backlight units have been mostly proposed and patented. Representative of these structures are a parallel side-by-side arrangement of R (red), G (green), B (blue) light emitting units, a vertical stacked arrangement of R GB light emitting units, and a Color Conversion Material (CCM) structure in which electroluminescence from a blue (B) organic light emitting layer and photoluminescence from inorganic light emission using electroluminescence are combined. The invention is applicable to these WOLEDs.
Further, the organic electronic element according to an embodiment of the present invention may be an Organic Light Emitting Diode (OLED), an organic solar cell, an Organic Photoconductor (OPC), an organic transistor (organic TFT), and an element for monochromatic or white illumination.
Another embodiment of the present invention provides an electronic device including a display apparatus having the above-described organic electronic element and a control unit for controlling the display apparatus. Here, the electronic device may be a wired/wireless communication terminal that is currently in use or will be used in the future, and cover various electronic devices including mobile communication terminals such as cellular phones, Personal Digital Assistants (PDAs), electronic dictionaries, point-to-multipoint (PMP), remote controllers, navigation units, game machines, various TVs, and various computers.
Hereinafter, a compound according to an aspect of the present invention will be described.
A compound according to one aspect of the present invention is represented by formula 1 below.
[ formula 1]
Figure BDA0001164304760000081
In the formula 1, the first and second groups,
m is an integer of 0 to 4.
R1Can be selected from deuterium, halogen, C6-C60Aryl, fluorenyl, C containing at least one heteroatom selected from O, N, S, Si and P2-C60Heterocyclic group, C3-C60Aliphatic radical and C6-C60Condensed ring radical of aromatic radical, C1-C50Alkyl radical, C2-C20Alkenyl radical, C2-C20Alkynyl, C1-C30Alkoxy and C6-C30Aryloxy groupGroup consisting of wherein when m is an integer of 2 or more, a plurality of R1May be the same as or different from each other.
Or, when m is an integer of 2 or more, a plurality of R1May be the same or different from each other and may be combined with each other to form at least one ring. Here, R which does not form a ring may be defined as above1。
X is O or S.
Y1And Y4Each independently is CRaOr N.
Y2And Y3Each independently is CRbOr N.
However, Y1And Y4Is N, and Y2And Y3Is N.
RaMay be selected from hydrogen, deuterium and-L1-Ar1Group (d) of (a).
RbMay be selected from hydrogen, deuterium and-L2-Ar2Group (d) of (a).
Ar1And Ar2Each of which may be independently selected from the group consisting of C6-C60Aryl, fluorenyl, C3-C60Aliphatic radical and C6-C60Condensed cyclic group of aromatic group, C containing at least one hetero atom selected from O, N, S, Si and P2-C60Heterocyclic group, C1-C50Alkyl radical, C2-C20Alkenyl radical, C2-C20Alkynyl, C1-C30Alkoxy and C6-C30Aryloxy groups.
L1And L2Each independently selected from the group consisting of a single bond, C6-C60Arylene, fluorenylene, C containing at least one heteroatom selected from O, N, S, Si and P2-C60Divalent heterocyclic group, C3-C60Aliphatic radical and C6-C60Divalent fused cyclic group of aromatic group, divalent aliphatic hydrocarbon group, wherein L1And L2(excluding single bonds) may each be taken from at least one substituent selected from the group consisting of deuterium, halogenSilyl, siloxane, boron, germanium, cyano, nitro, C1-C20Alkylthio radical, C1-C20Alkoxy radical, C1-C20Alkyl radical, C2-C20Alkenyl radical, C2-C20Alkynyl, C6-C20Aryl, C substituted by deuterium6-C20Aryl, fluorenyl, C2-C20Heterocyclic group, C3-C20Cycloalkyl radical, C7-C20Arylalkyl and C8-C20Arylalkenyl groups. Here, a single bond means a direct bond due to the absence of L1And L2And formulae 1-1, 1-78, etc., which may be included in chemical formula 1 of the present invention, represent wherein L1Compounds which are single bonds, and formulas 1 to 89, 1 to 117 and the like which may be included in chemical formula 1 of the present invention represent wherein L2A compound which is a single bond.
For example, when Ar1And Ar2When it is aryl, Ar1And Ar2Each independently may be phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, pyrenyl, benzophenanthrenyl, and the like. In addition, L1And L2When it is arylene, L1And L2May each independently be phenylene, biphenylene, terphenylene, naphthylene, anthracenylene, phenanthrenylene, pyrenylene, triphenylene, or the like.
R1、Ar1And Ar2Each of the aryl group, the fluorenyl group, the heterocyclic group, the fused group (fusion group), the alkyl group, the alkenyl group, the alkoxy group, and the aryloxy group of (a) may be substituted with at least one substituent selected from the group consisting of: deuterium, halogen, silyl, siloxane, boron, germanium, cyano, nitro, C1-C20Alkylthio radical, C1-C20Alkoxy radical, C1-C20Alkyl radical, C2-C20Alkenyl radical, C2-C20Alkynyl, C6-C20Aryl, C substituted by deuterium6-C20Aryl, fluorenyl, C2-C20Heterocyclic group, C3-C20CycloalkanesBase, C7-C20Arylalkyl and C8-C20An arylalkenyl group.
Here, the aryl group may be an aryl group having 6 to 60 carbon atoms, preferably 6 to 40 carbon atoms, more preferably 6 to 30 carbon atoms;
the heterocyclic group may be a heterocyclic group having 2 to 60 carbon atoms, preferably 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms;
the arylene group may be an arylene group having 6 to 60 carbon atoms, preferably 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms; and
the alkyl group may be an alkyl group having 1 to 50 carbon atoms, preferably 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 10 carbon atoms.
In particular, the compound represented by the above formula 1 may be represented by one of the following formulas.
Figure BDA0001164304760000101
In the above formulas 2 and 3, X, R1、Ar1、Ar2、L1、L2And m may be as defined in formula 1.
Specifically, Ar in the compounds represented by the above formulas 1 to 31And Ar2May be independently represented by one of formulae a1 to A8 below.
Figure BDA0001164304760000111
In formulae a1 to A8,
n is an integer of 0 to 4; o is an integer from 0 to 5;
p is an integer from 0 to 6; r is an integer from 0 to 8.
Q1To Q11Each independently is CRcOr N.
Q12To Q15Each independently is C, CRdOr N.
W is S, O, NReOr CRfRg。
R2Can be selected from deuterium, halogen, C6-C60Aryl, fluorenyl, C containing at least one heteroatom selected from O, N, S, Si and P2-C60Heterocyclic group, C3-C60Aliphatic radical and C6-C60Condensed ring radical of aromatic radical, C1-C50Alkyl radical, C2-C20Alkenyl radical, C2-C20Alkynyl, C1-C30Alkoxy and C6-C30Aryloxy group, wherein when n, o, p and R are each an integer of 2 or more, a plurality of R2May be the same as or different from each other.
Or, when n, o, p and R are each an integer of 2 or more, a plurality of R2May be the same or different from each other and may be combined with each other to form at least one ring. Here, R which does not form a ring may be defined as above2。
RcAnd RdEach independently selected from hydrogen, deuterium, C6-C60Aryl, fluorenyl, C3-C60Aliphatic radical and C6-C60Fused ring radical of an aromatic radical, C containing at least one heteroatom selected from O, N, S, Si and P2-C60Heterocyclic group, C1-C50Alkyl radical, C2-C20Alkenyl radical, C2-C20Alkynyl, C1-C30Alkoxy and C6-C30Aryloxy group; rcAnd RdEach of which may be substituted with at least one substituent selected from the group consisting of deuterium, halogen, silyl, siloxane, boron, germanium, cyano, nitro, C1-C20Alkylthio radical, C1-C20Alkoxy radical, C1-C20Alkyl radical, C2-C20Alkenyl radical, C2-C20Alkynyl, C6-C20Aryl, C substituted by deuterium6-C20Aryl, fluorenyl, C2-C20Heterocyclic group, C3-C20Cycloalkyl radical, C7-C20Arylalkyl and C8-C20Aryl alkenyl groups.
ReTo RgEach of which may be independently selected from the group consisting of C6-C60Aryl radical, C containing at least one heteroatom chosen from O, N, S, Si and P2-C60Heterocyclic group, C1-C50Alkyl radical, C2-C20Alkenyl radical, C1-C30Alkoxy groups and fluorenyl groups.
Symbol represents and L1Or L2The connection of (2).
More specifically, the compound represented by formulae 1 to 3 may be one of the following compounds.
Figure BDA0001164304760000121
Figure BDA0001164304760000131
Figure BDA0001164304760000141
Figure BDA0001164304760000151
Figure BDA0001164304760000161
Figure BDA0001164304760000171
Figure BDA0001164304760000181
Figure BDA0001164304760000191
Figure BDA0001164304760000201
Figure BDA0001164304760000211
Figure BDA0001164304760000221
Figure BDA0001164304760000231
Figure BDA0001164304760000241
Figure BDA0001164304760000251
Figure BDA0001164304760000261
Figure BDA0001164304760000271
Figure BDA0001164304760000281
According to another embodiment, the present invention provides a compound for an organic electronic element represented by formula 1.
According to another embodiment, the present invention provides an organic electronic element comprising the compound represented by formula 1.
Here, the organic electronic element may include: a first electrode; a second electrode; and an organic material layer disposed between the first electrode and the second electrode. The organic material layer may include the compound represented by formula 1, and the compound represented by formula 1 may be included in at least one of a hole injection layer, a hole transport layer, an auxiliary light emitting layer, or a light emitting layer and an electron transport layer of the organic material layer. In particular, the compound represented by formula 1 may be included in the light emitting layer and the electron transport layer.
That is, the compound represented by formula 1 may be used as a material for a hole injection layer, a hole transport layer, an auxiliary light emitting layer, a light emitting layer, an electron transport layer, or an electron injection layer. Specifically, the present invention provides an organic electronic element containing one of the compounds represented by formula 2 or formula 3 in an organic material layer, and more specifically, an organic electronic device containing the compound represented by each of chemical formulas (1-1 to 1-201 and 2-1 to 2-110) in an organic material layer.
In another embodiment, the present invention provides an organic electronic element, wherein the compound comprises two or more different compounds alone, as a combination, or the compound is contained together with another compound in combination of two or more in at least one of a hole injection layer, a hole transport layer, an auxiliary light emitting layer, a light emitting layer, an electron transport layer, and an electron injection layer in an organic material layer. In other words, the compounds corresponding to formulas 1 to 3 may be contained individually in each layer; two or more compounds of the formulae 1 to 3 may be contained in each layer or a mixture of compounds according to claims 1 to 4 and compounds not corresponding to the invention may be contained. Here, the compound not corresponding to the present invention may be a single compound or two or more compounds. Here, when the compound is combined with another compound as a combination of two or more compounds, the other compound may be a compound known for each organic material layer or a compound developed in the future. Here, the compounds contained in the organic material layer may consist of only the same kind of compounds, or a mixture of two or more different compounds represented by formula 1.
In another embodiment of the present invention, the present invention provides an organic electronic element further comprising a light efficiency improving layer formed on at least one of a side of one surface of the first electrode opposite to the organic material layer and a side of one surface of the second electrode opposite to the organic material layer.
Hereinafter, a synthesis embodiment of the compound represented by formula 1 and a manufacturing embodiment of the organic electronic element according to the present invention will be described in detail by embodiments. However, the following embodiments are for illustrative purposes only and are not intended to limit the scope of the present invention.
[ Synthesis embodiment ]
The final product represented by formula 1 according to the present invention is synthesized through the reaction pathways of reaction scheme 1 and reaction scheme 2, but is not limited thereto.
< reaction scheme 1>
Figure BDA0001164304760000301
< reaction scheme 2>
Figure BDA0001164304760000302
X、R1、Ar1、Ar2、L1、L2And m is as defined in claim 1.
Synthesis of Sub 1A and Sub 1B
The Sub 1A and Sub 1B of the above reaction scheme 1 can be synthesized by the reaction routes of reaction scheme 3 and reaction scheme 4, but are not limited thereto.
< reaction scheme 3>
Figure BDA0001164304760000303
< reaction scheme 4>
Figure BDA0001164304760000304
An embodiment for the synthesis of a specific compound belonging to Sub 1 is as follows.
Synthesis embodiment of Sub 1A-1
< reaction scheme 5>
Figure BDA0001164304760000311
In a round-bottom flask, the starting material 2, 4-dichlorobenzo [4, 5]]Thieno [3,2-d]Pyrimidine (70.84g, 277.7mmol) was dissolved in THF, and Sub 2-136(62.33g, 305.4mmol), Pd (PPh) were added thereto3)4(12.83g，11.1mmol)、K2CO3(115.13g, 833mmol) and water, then stirred at 90 ℃. After the reaction is completed, use CH2Cl2And water extraction of the reaction product. The organic layer was MgSO4Drying and concentration, followed by subjecting the resulting compound to a silica gel column and recrystallization, gave 36.26g of the product (yield: 44%).
Synthesis embodiment of Sub 1A-9
< reaction scheme 6>
Figure BDA0001164304760000312
Except that 2, 4-dichlorobenzo [4, 5] is used as the starting material]Thieno [3,2-d]Pyrimidine (9.96g, 39mmol), Synthesis of Sub 1A-1 Using Sub2-146 (13.06g, 42.9mmol), Pd (PPh)3)4(1.8g，1.6mmol)、K2CO3(16.19g, 117.1mmol), THF and water gave 7.13g of product (yield: 46%).
Synthetic embodiment of Sub 1A-16
< reaction scheme 7>
Figure BDA0001164304760000321
Except that 2, 4-dichlorobenzo [4, 5] is used as the starting material]Thieno [3,2-d]Pyrimidine (9.87g, 38.7mmol), Synthesis method according to Sub 1A-1 Using Sub2-1 (18.53g, 42.6mmol), Pd (PPh)3)4(1.79g，1.5mmol)、K2CO3(16.04g, 116.1mmol), THF and water, to give 8.58g of a product (yield: 42%).
Synthesis embodiment of Sub 1A-60
< reaction scheme 8>
Figure BDA0001164304760000322
Except that 2, 4-dichlorobenzofuran [3,2-d ] is used as the starting material]Pyrimidine (8.51g, 35.6mmol), Synthesis method according to Sub 1A-1 Using Sub2-88 (19.91g, 39.2mmol), Pd (PPh)3)4(1.65g，1.4mmol)、K2CO3(14.76g, 106.8mmol), THF and water, to give 8.12g of a product (yield: 39%).
Synthesis embodiment of Sub 1B-1
< reaction scheme 9>
Figure BDA0001164304760000323
Except that 2, 4-dichlorobenzo [4, 5] is used as the starting material]Thieno [2,3-d ]]Pyrimidine (19.78g, 77.5mmol), Synthesis method according to Sub 1A-1 Using Sub 2-136(17.4g, 85.3mmol), Pd (PPh)3)4(3.58g，3.1mmol)、K2CO3(32.15g, 232.6mmol), THF and water to give 10.81g of the product (yield: 47%).
Synthesis embodiment of Sub 1B-38
< reaction scheme 10>
Figure BDA0001164304760000331
Except that 2, 4-dichlorobenzofuran [2,3-d ] is used as a starting material]Pyrimidine (9.06g, 37.9mmol), Synthesis method according to Sub 1A-1 Using Sub 2-136(8.51g, 41.7mmol), Pd (PPh)3)4(1.75g，1.5mmol)、K2CO3(15.71g, 113.7mmol), THF and water, 5.11g of the product were obtained (yield: 48%).
Synthesis embodiment of Sub 1B-43
< reaction scheme 11>
Figure BDA0001164304760000332
Except that 2, 4-dichlorobenzofuran [2,3-d ] is used as a starting material]Pyrimidine (13.23g, 55.3mmol), Synthesis method according to Sub 1A-1 Using Sub 2-164(31.07g, 60.9mmol), Pd (PPh)3)4(2.56g，2.2mmol)、K2CO3(22.95g, 166mmol), THF and water, to give 13.97g of a product (yield: 43%).
The compounds belonging to Sub 1A and Sub 1B may be the following compounds, but are not limited thereto. Table 1 shows FD-MS values of the compounds belonging to Sub 1A and Sub 1B
Figure BDA0001164304760000341
Figure BDA0001164304760000351
Figure BDA0001164304760000361
[ Table 1]
Figure BDA0001164304760000371
Figure BDA0001164304760000381
Synthesis of sub2
The Sub2 of reaction scheme 1 above can be synthesized by the reaction pathways of reaction scheme 12 and reaction scheme 13, but is not limited thereto.
< reaction scheme 12>
Figure BDA0001164304760000382
< reaction scheme 13>
Figure BDA0001164304760000391
Ar and L are as defined below, and Hal is Br or Cl.
Figure BDA0001164304760000392
An embodiment of the synthesis of a specific compound belonging to Sub2 is as follows.
Synthesis embodiment of Sub2-1
< reaction scheme 14>
Figure BDA0001164304760000393
The starting material 2-chloro-4, 6-diphenyl-1, 3, 5-triazine (42.86g, 160.1mmol) was dissolved in THF in a round-bottomed flask, and 1,4-bis (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) benzene (1,4-bis (4,4,5, 5-tetramethy-1, 3,2-dioxaborolan-2-yl) bezene) (58.12g, 176.1mmol), Pd (PPh)3)4(7.4g，6.4mmol)、K2CO3(66.38g, 480.3mmol) and water, followed by stirring at 80 ℃. After the reaction is finished, the reaction product is treated with CH2Cl2And water extraction. The organic layer was MgSO4Drying and concentration, then subjecting the obtained compound to a silica gel column and recrystallization, gave 28.58g of the product (yield: 41%).
Synthesis embodiment of Sub2-13
< reaction scheme 15>
Figure BDA0001164304760000401
Starting material 2- (5-bromo-5 '-phenyl- [1, 1': 3', 1' -terphenyl) was placed in a round bottom flask]-3-yl) -4, 6-diphenyl-1, 3, 5-triazine (17.92g, 29.1mmol) was dissolved in DMF, and then bis (pinacolato) diboron (8.12g, 32mmol), Pd (dppf) Cl was added thereto2(0.71g, 0.9mmol), KOAc (8.56g, 87.2mmol), followed by stirring at 90 ℃. After completion of the reaction, DMF was removed by distillation and then taken up with CH2Cl2And water extraction. The organic layer was MgSO4Drying and concentration, then the obtained compound was subjected to silica gel column and recrystallization to obtain 11.38g (yield: 59%).
Synthetic embodiment of Sub2-15
< reaction scheme 16>
Figure BDA0001164304760000402
In addition to 2- (3-bromo-5- (phenanthren-2-yl) phenyl) -4, 6-diphenyl-1, 3, 5-triazine (16.53g, 29.3mmol) as starting material, bis (pinacolato) diboron (8.18g, 32.2mmol), Pd (dppf) Cl was used under the synthesis method of Sub2-132(0.72g, 0.9mmol), KOAc (8.62g, 87.9mmol) and DMF to give 10.92g of the product (yield: 61%).
Synthesis embodiment of Sub2-42
< reaction scheme 17>
Figure BDA0001164304760000411
Except that 4, 6-bis ([1,1' -biphenyl ] yl) is used as the starting material]-3-yl) -2-chloropyrimidine (17.21g, 41.1mmol) synthesized according to the method of Sub2-1 using 1,4-bis (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) benzene (14.91g, 45.2mmol), Pd (PPh)3)4(1.9g，1.6mmol)、K2CO3(17.03g, 123.2mmol), THF and water, 9.16g of product were obtained (yield 38%).
Synthetic embodiment of Sub2-88
< reaction scheme 18>
Figure BDA0001164304760000412
In addition to 2-chloro-4- (phenanthren-9-yl) quinazoline (54.73g, 160.6mmol) as a starting material, 1,4-bis (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) benzene (58.3g, 176.6mmol), Pd (PPh) were used according to the synthesis method of Sub2-13)4(7.42g，6.4mmol)、K2CO3(66.58g，481.8mmol), THF and water to give 29.39g of product (yield: 36%).
Synthetic embodiment of Sub2-133
< reaction scheme 19>
Figure BDA0001164304760000413
Except that 9- (3 '-bromo- [1,1' -biphenyl) is used as starting material]-3-yl) phenanthrene (11.28g, 27.6mmol) bis (pinacolato) diboron (7.7g,30.3mmol), Pd (dppf) Cl was used in accordance with the synthesis of Sub2-132(0.68g, 0.8mmol), KOAc (8.11g, 82.7mmol) and DMF to give 8.55g of the product (yield: 68%).
Synthetic embodiments of Sub2-135
< reaction scheme 20>
Figure BDA0001164304760000421
Except that 2- (3 '-bromo- [1,1' -biphenyl) is used as the starting material]-3-yl) triphenylene (13.49g, 29.4mmol), according to the synthesis of Sub2-13 using bis (pinacolato) diboron (8.2g, 32.3mmol), Pd (dppf) Cl2(0.72g, 0.9mmol), KOAc (8.65g, 88.1mmol) and DMF to give 9.52g of the product (yield: 64%).
Synthetic embodiment of Sub 2-136
< reaction scheme 21>
Figure BDA0001164304760000422
In addition to bromobenzene (88.71g, 565mmol) as starting material, bis (pinacolato) diboron (157.82g, 621.5mmol), Pd (dppf) Cl was used in accordance with the synthesis of Sub2-132(13.84g, 16.9mmol), KOAc (166.35g, 1695mmol) and DMF to give 99.16g of the product (yield: 86%).
Synthetic embodiments of Sub2-146
< reaction scheme 22>
Figure BDA0001164304760000423
In addition to 9-bromophenanthrene (21.04g, 81.8mmol) as a starting material, bis (pinacolato) diboron (22.86g, 90mmol), Pd (dppf) Cl were used in accordance with the synthesis method of Sub2-132(2g, 2.5mmol), KOAc (24.09g, 245.5mmol) and DMF to give 18.17g of product (yield: 73%).
Synthetic embodiments of Sub2-162
< reaction scheme 23>
Figure BDA0001164304760000431
In addition to 3- (3-bromo-5- (phenanthren-9-yl) phenyl) pyridine (26.32g, 64.1mmol) as a starting material, bis (pinacolato) diboron (17.92g, 70.6mmol), Pd (dppf) Cl was used in accordance with the synthesis method of Sub2-132(1.57g, 1.9mmol), KOAc (18.89g, 192.4mmol) and DMF to give 16.72g of the product (yield: 57%).
Synthetic embodiments of Sub 2-164
< reaction scheme 24>
Figure BDA0001164304760000432
Except that 2,2' - (5' -bromo- [1,1 ': 3', 1' -terphenyl)]-4,4 "-diyl) bipyridine (41.36g, 89.3mmol), according to the synthesis of Sub2-13 using bis (pinacolato) diboron (24.93g, 98.2mmol), Pd (dppf) Cl2(2.19g, 2.7mmol), KOAc (26.28g, 267.8mmol) and DMF to give 34.17g of the product (yield: 75%).
The compound belonging to Sub2 may be the following compound, but is not limited thereto. The FD-MS values of the compounds belonging to Sub2 are shown in table 2 below.
Figure BDA0001164304760000441
Figure BDA0001164304760000451
Figure BDA0001164304760000461
Figure BDA0001164304760000471
Figure BDA0001164304760000481
[ Table 2]
Figure BDA0001164304760000482
Figure BDA0001164304760000491
Figure BDA0001164304760000501
Figure BDA0001164304760000511
III product Synthesis
In a round bottom flask Sub 1A or Sub 1B (1 equiv.) was dissolved in THF, then Sub2(1 equiv.), Pd (PPh) were added3)4(0.04 eq), NaOH (3 eq), and water, then stirred at 75 ℃. After the reaction is finished, the reaction product is treated with CH2Cl2And water extraction. The organic layer was washed with MgSO4Drying and concentration, then subjecting the resulting compound to a silica gel column and recrystallization to give the final product.
1. Synthesis embodiments 1 to 1:
< reaction scheme 25>
Figure BDA0001164304760000521
Sub 1A-1(5.45g, 18.4mmol) obtained in the above synthesis was dissolved in THF in a round-bottomed flask, followed by addition of Sub2-1 (7.99g, 18.4mmol), Pd (PPh)3)4(0.85g, 0.7mmol), NaOH (2.2g, 55.1mmol) and water, stirred at 75 ℃. After the reaction is finished, the reaction product is treated with CH2Cl2And water extraction. The organic layer was MgSO4Drying and concentration, followed by subjecting the resulting compound to a silica gel column and recrystallization, gave 7.43g of the product (yield: 71%).
2. Synthesis embodiments 1 to 25:
< reaction scheme 26>
Figure BDA0001164304760000522
In addition to Sub 1A-1(4.04g, 13.6mmol) obtained from the above synthesis, Sub2-42(7.98g, 13.6mmol), Pd (PPh) were used in accordance with the method for the synthesis of 1-13)4(0.63g, 0.5mmol), NaOH (1.63g, 40.8mmol), THF and water, 6.77g of the product was obtained (yield: 69%).
3. Synthesis embodiments 1 to 43:
< reaction scheme 27>
Figure BDA0001164304760000523
In addition to Sub 1A-1(4.7g, 15.8mmol) obtained from the above synthesis, Sub2-88(8.05g, 15.8mmol), Pd (PPh) was used according to the method for the synthesis of 1-13)4(0.73g, 0.6mmol), NaOH (1.9g, 47.5mmol), THF and water to give 6.82g of the product (yield: 67%).
4. Synthesis embodiments 1-86:
< reaction scheme 28>
Figure BDA0001164304760000531
In addition to Sub 1A-9(6.9g, 17.4mmol) obtained from the above synthesis, Sub2-162(7.65g, 17.4mmol), Pd (PPh) were used according to the method for the synthesis of 1-13)4(0.8g, 0.7mmol), NaOH (2.09g, 52.2mmol), THF and water to give 7.82g of the product (yield: 65%).
5. Synthesis embodiments 1-117:
< reaction scheme 29>
Figure BDA0001164304760000532
In addition to Sub 1A-16(8.37g, 15.9mmol) obtained from the above synthesis, Sub 2-136(3.23g, 15.9mmol), Pd (PPh), was used according to the method for the synthesis of 1-13)4(0.73g, 0.6mmol), NaOH (1.9g, 47.6mmol), THF and water to give 6.59g of a product (yield: 73%).
6. Synthesis embodiments 1-142:
< reaction scheme 30>
Figure BDA0001164304760000533
In addition to Sub 1A-60(7.72g, 13.2mmol) obtained from the above synthesis, Sub2-146(4.01g, 13.2mmol), Pd (PPh) were used according to the method for the synthesis of 1-13)4(0.61g, 0.5mmol), NaOH (1.58g, 39.6mmol), THF and water to give 6.14g of the product (yield: 64%).
7. Synthesis embodiments 1-161:
< reaction scheme 31>
Figure BDA0001164304760000541
In addition to Sub 1A-1(4.83g, 16.3mmol) obtained from the above synthesis, Sub2-135(8.24g, 16.3mmol), Pd (PPh) were used according to the method for the synthesis of 1-13)4(0.75g, 0.7mmol), NaOH (1.95g, 48.8mmol), THF and water to give 6.88g of the product (yield: 66%).
8. Synthesis embodiments 1-166:
< reaction scheme 32>
Figure BDA0001164304760000542
In addition to Sub 1A-1(4.64g, 15.6mmol) obtained by the above synthesis, Sub2-13(10.38g, 15.6mmol), Pd (PPh) were used according to the method for the synthesis of 1-13)4(0.72g, 0.6mmol), NaOH (1.88g, 46.9mmol), THF and water to give the product 8.48g (yield: 68%).
9. Synthesis embodiments 2 to 48:
< reaction scheme 33>
Figure BDA0001164304760000551
In addition to Sub 1B-1(4.99g, 16.8mmol) obtained from the above synthesis, Sub2-133(7.67g, 16.8mmol), Pd (PPh) were used according to the method for the synthesis of 1-13)4(0.78g, 0.7mmol), NaOH (2.02g, 50.4mmol), THF and water to give 6.65g of the product (yield: 67%).
10. Synthesis embodiments 2-69:
< reaction scheme 34>
Figure BDA0001164304760000552
In addition to Sub 1B-1(4.64g, 15.6mmol) obtained from the above synthesis, Sub2-15(9.56g, 15.6mmol), Pd (PPh) were used according to the method for the synthesis of 1-13)4(0.72g, 0.6mmol), NaOH (1.88g, 46.9mmol), THF and water to give 7.58g of the product (yield: 65%).
11. Synthesis embodiments 2-103:
< reaction scheme 35>
Figure BDA0001164304760000553
In addition to Sub 1B-38(4.83g, 17.2mmol) obtained from the above synthesis, Sub2-162 (7.87g, 17.2mmol), Pd (PPh), was used according to the method for the synthesis of 1-13)4(0.8g, 0.7mmol), NaOH (2.06g, 51.6mmol), THF and water to give 6.64g of a product (yield: 67%).
12. Synthesis embodiments 2-109:
< reaction scheme 36>
Figure BDA0001164304760000561
In addition to Sub 1B-43(11.86g, 20.2mmol) obtained from the above synthesis, Sub 2-136(4.12g, 20.2mmol), Pd (PPh) were used according to the method for the synthesis of 1-13)4(0.93g, 0.8mmol), NaOH (2.42g, 60.6mmol), THF and water to give 7.37g of the product (yield: 58%).
Meanwhile, FD-MS values of the compounds 1-1 to 2-110 according to an embodiment of the present invention prepared according to the above synthesis embodiments are shown in table 3 below.
[ Table 3]
Figure BDA0001164304760000562
Figure BDA0001164304760000571
Figure BDA0001164304760000581
Figure BDA0001164304760000591
Figure BDA0001164304760000601
Figure BDA0001164304760000611
Meanwhile, synthetic embodiments of the present invention represented by formula 1 have been described, but these embodiments are based on Suzuki cross-coupling reaction and Miyaura boration reaction. Those skilled in the art will readily appreciate that other than the substitutions specified in the specific synthetic embodimentsOther than the substituents, i.e. other substituents (X, R) as defined in formula 11、Ar1、Ar2、L1、L2And m) are combined, the above reaction still proceeds. For example, all of the reactions of the starting material → Sub 1A in reaction scheme 3, the starting material → Sub 1B in reaction scheme 4, and the starting material → Sub2 in reaction scheme 12, and the reactions in reaction schemes 25 to 36 are based on Suzuki cross-coupling reactions; the starting material → Sub2 reaction in reaction scheme 13 is based on Miyaura boration. The above reaction proceeds even if unspecified substituents are bonded thereto.
Production and evaluation of organic electronic Components
[ embodiment I-1]Green organic electronic luminous element (electronic transmission layer)
An organic electronic light-emitting element was manufactured by a conventional method using the compound according to an embodiment of the present invention as a material of an electron transport layer. First, 4' -tris [ 2-naphthyl (phenyl) amino group was vacuum-deposited on an ITO layer (anode) formed on a glass substrate]Triphenylamine (hereinafter, referred to as "2-TNATA") to form a hole injection layer having a thickness of 60nm, and then, 4' -bis (N- (1-naphthyl) -N-phenylamino) was vacuum-deposited on the hole injection layer]Biphenyl (hereinafter abbreviated as "NPD") forms a hole transport layer having a thickness of 60 nm. Next, 4'-N, N' -dicarbazolebiphenyl (hereinafter referred to as "CBP") as a host material and tris (2-phenylpyridine) -iridium (hereinafter referred to as "Ir (ppy") as a dopant material3") was doped at a weight ratio of 95:5 to form a light emitting layer having a thickness of 30nm on the hole transport layer. Then, (1,1' -biphenyl) -4-Hydroxy) bis (2-methyl-8-hydroxyquinoline) Aluminum ((1, 1' -biphenyl) -4-olato) bis (2-methyl-8-quinonolato) aluminum) (hereinafter, abbreviated as "BAlq") to form a hole blocking layer on the light emitting layer, and the compound 1-1 of the present invention according to an embodiment of the present invention was vacuum-deposited at a thickness of 40nm to form an electron transporting layer on the hole blocking layer. Then, LiF as a halogenated alkali metal was deposited in a thickness of 0.2nm to form an electron injection layer on the electron transport layer, and then deposited in a thickness of 150nmAl to form the cathode. Through the above procedure, an organic electronic light-emitting element was manufactured.
[ embodiment I-2]To [ embodiment I-166]Green organic electronic luminous element (electronic transmission layer)
An organic electronic light-emitting element was manufactured by the same method as embodiment I-1, except that compounds 1-2 to 2-110 according to an embodiment of the present invention listed in table 4 below were used instead of compound 1-1 according to an embodiment of the present invention as the material of the electron transport layer.
Comparative example I-1]
An organic electroluminescent element was fabricated by the same method as embodiment I-1, except that the following comparative compound 1 was used as a material of the electron transport layer instead of the compound 1-1 according to the embodiment of the present invention.
Comparative example I-2]
An organic electroluminescent element was fabricated by the same method as embodiment I-1, except that the following comparative compound I-2 was used instead of the compound 1-1 according to the embodiment of the present invention as a material of the electron transport layer.
Comparative examples I to 3]
An organic electroluminescent element was fabricated by the same method as embodiment I-1, except that the following comparative compound I-3 was used instead of the compound 1-1 according to the embodiment of the present invention as a material of the electron transport layer.
Comparative examples I to 4]
An organic electroluminescent element was fabricated by the same method as embodiment I-1, except that the following comparative compound I-4 was used instead of the compound 1-1 according to the embodiment of the present invention as a material of the electron transport layer.
Comparative examples I to 5]
An organic electroluminescent element was fabricated by the same method as embodiment I-1, except that the following comparative compound I-5 was used instead of the compound 1-1 according to the embodiment of the present invention as a material of the electron transport layer.
Comparative examples I to 6]
An organic electroluminescent element was fabricated by the same method as embodiment I-1, except that the following comparative compound I-6 was used instead of the compound 1-1 according to the embodiment of the present invention as a material of the electron transport layer.
Comparative examples I to 7]
An organic electroluminescent element was fabricated by the same method as embodiment I-1, except that the following comparative compound I-7 was used instead of the compound 1-1 according to the embodiment of the present invention as a material of the electron transport layer.
Comparative examples I to 8]
An organic electroluminescent element was fabricated by the same method as embodiment I-1, except that the following comparative compound I-8 was used instead of the compound 1-1 according to the embodiment of the present invention as a material of the electron transport layer.
Comparative examples I to 9]
An organic electroluminescent element was fabricated by the same method as embodiment I-1, except that the following comparative compound I-9 was used instead of the compound 1-1 according to the embodiment of the present invention as a material of the electron transport layer.
Figure BDA0001164304760000641
A forward bias DC voltage was applied to each of the organic electroluminescent elements fabricated in embodiments I-1 to I-166 and comparative examples I-1 to I-9, and its Electroluminescent (EL) characteristics were measured by PR-650 (Photoresearch). In addition, at 5000cd/m2The life of T95 was measured by a life measuring device (Mcscience). The measurement results are shown in table 4 below.
[ Table 4]
Figure BDA0001164304760000651
Figure BDA0001164304760000661
Figure BDA0001164304760000671
Figure BDA0001164304760000681
Figure BDA0001164304760000691
Figure BDA0001164304760000701
Figure BDA0001164304760000711
Figure BDA0001164304760000721
As shown in Table 4 above, the organic electroluminescent element measured using the material for organic electroluminescent elements of the present invention compares the compounds I-1, Alq with the existing materials that have been widely used as electron transport layers3Compared with the prior art, the high-efficiency high-voltage LED display panel has the advantages of low driving voltage, high efficiency and long service life. The reason is determined to be, although Alq for the electron transport layer3T of1Significantly lower value than Ir (ppy) used as dopant in the light emitting layer3T of1Values, however, Compounds according to embodiments of the invention exhibit ratios to Ir (ppy)3Generally higher T1Value, resulting in a relative increase in the probability of excitons residing in the light-emitting layer.
As for the results of the organic electronic light emitting elements of the compounds according to the embodiment of the present invention and the comparative compounds I-2 to I-9, it can be confirmed that the compounds according to the embodiment of the present invention show a low driving voltage and a remarkably high efficiency and a high lifetime as compared with the comparative compounds I-2 to I-9. The reason is determined that, even with thienopyrimidine or furopyrimidine cores similar to the compounds according to the embodiments of the present invention, comparative compounds I-2 and I-9 without a fused benzene ring have significantly lower LUMO values than the compounds of the embodiments of the present invention with a fused benzene ring, thereby relatively decreasing the electron transport ability. However, as in the compounds according to the embodiments of the present invention, the fusion of the benzene ring to the thienopyrimidine or furopyrimidine core allows high thermal stability, a relatively low driving voltage by adjusting the bulk density between materials, and relatively efficient electron transport due to an increase in LUMO value compared to the comparative compound, thereby obtaining charge balance of holes and electrons, and forming light emission within the light emitting layer rather than at the interface of the electron transport layer, and as a result, it can be confirmed that the compounds according to the embodiments of the present invention show high efficiency and lifetime compared to the comparative compounds I-1 to I-9.
Furthermore, it is necessary to consider the correlation between the electron transport layer and the light emitting layer (host), and therefore, although similar cores are used, those skilled in the art will have great difficulty even in obtaining the characteristics of the electron transport layer using the compound according to the present invention.
[ embodiment II-1]Green organic electronic luminous element (phosphorescent main body for luminous layer)
An organic electronic light-emitting element is manufactured by a conventional method using the compound according to an embodiment of the present invention as a phosphorescent material. First, 2-TNATA was vacuum-deposited on an ITO layer (anode) formed on a glass substrate at a thickness of 60nm to form a hole injection layer, and then NPD was vacuum-deposited on the hole injection layer at a thickness of 60nm to form a hole transport layer. Subsequently, compound 1-1 as a host material and Ir (ppy) as a dopant material were doped in a weight ratio of 95:53To form a light-emitting layer with a thickness of 30nm on the hole transport layer. Then, BAlq was vacuum-deposited at a thickness of 10nm to form a hole blocking layer on the light-emitting layer, and tris (8-quinolinolato) aluminum (hereinafter referred to as "Alq" for short) was vacuum-deposited at a thickness of 40nm3") to form an electron transport layer on the hole blocking layer. Then, LiF as a halogenated alkali metal was deposited in a thickness of 0.2nm to form an electron injection layer on the electron transport layer, and then Al was deposited in a thickness of 150nm to form a cathode. Thereby manufacturing an organic electroluminescent element。
[ embodiment II-2] to [ embodiment II-151] Green organic electroluminescent elements (phosphorescent host for light-emitting layer)
An organic electronic light-emitting element was manufactured by the same method as embodiment II-1, except that compounds 1-5 to 2-108 (listed in table 5 below) according to an embodiment of the present invention were used instead of compound 1-1 according to an embodiment of the present invention as the material of the host material of the light-emitting layer.
Comparative example II-1]
An organic electronic light-emitting element was manufactured by the same method as embodiment II-1, except that the following comparative compound II-1 was used instead of the compound 1-1 according to the embodiment of the present invention as a host material of the light-emitting layer.
Comparative example II-2]
An organic electronic light-emitting element was manufactured by the same method as embodiment II-1, except that the following comparative compound II-2 was used instead of the compound 1-1 according to the embodiment of the present invention as a host material of the light-emitting layer.
Comparative examples II to 3]
An organic electronic light-emitting element was manufactured by the same method as embodiment II-1, except that the following comparative compound II-3 was used instead of the compound 1-1 according to the embodiment of the present invention as a host material of the light-emitting layer.
Comparative examples II to 4]
An organic electronic light-emitting element was manufactured by the same method as embodiment II-1, except that the following comparative compound II-4 was used instead of the compound 1-1 according to the embodiment of the present invention as a host material of the light-emitting layer.
Comparative examples II to 5]
An organic electronic light-emitting element was manufactured by the same method as embodiment II-1, except that the following comparative compound II-5 was used instead of the compound 1-1 according to the embodiment of the present invention as a host material of the light-emitting layer.
[ comparative examples II-6]
An organic electronic light-emitting element was manufactured by the same method as embodiment II-1, except that the following comparative compound II-6 was used instead of the compound 1-1 according to the embodiment of the present invention as a host material of the light-emitting layer.
Comparative examples II to 7]
An organic electronic light-emitting element was manufactured by the same method as embodiment II-1, except that the following comparative compound II-7 was used instead of the compound 1-1 according to the embodiment of the present invention as a host material of the light-emitting layer.
Comparative examples II to 8]
An organic electronic light-emitting element was manufactured by the same method as embodiment II-1, except that the following comparative compound II-8 was used instead of the compound 1-1 according to the embodiment of the present invention as a host material of the light-emitting layer.
Comparative examples II to 9]
An organic electronic light-emitting element was manufactured by the same method as embodiment II-1, except that the following comparative compound II-9 was used instead of the compound 1-1 according to the embodiment of the present invention as a host material of the light-emitting layer.
Figure BDA0001164304760000751
A forward bias DC voltage was applied to each of the organic electroluminescent elements fabricated in embodiments II-1 to II-151 and comparative examples II-1 to II-9, and the Electroluminescent (EL) characteristics thereof were measured by PR-650 (Photoresearch). In addition, at 5000cd/m2The life of T95 was measured by a life measuring device (Mcscience). The measurement results are shown in table 5 below.
[ Table 5]
Figure BDA0001164304760000761
Figure BDA0001164304760000771
Figure BDA0001164304760000781
Figure BDA0001164304760000791
Figure BDA0001164304760000801
Figure BDA0001164304760000811
Figure BDA0001164304760000821
As can be seen from the results of Table 5 above, comparative example (II-1) using the existing phosphorescent host material CBP, which has been widely used at present, shows a tendency of high driving voltage, low efficiency and low lifetime, and comparative examples (II-2) to (II-9) using a compound having a thienopyrimidine or furopyrimidine core show gradually good results in terms of both efficiency and lifetime, as compared to comparative example (II-1). However, sufficiently good characteristics having a large influence on the element are not exhibited. However, the compounds according to embodiments of the present invention containing two nitrogen (N) atoms on the thienopyrimidine or furopyrimidine core showed lower driving voltage, higher efficiency and higher lifetime than the comparative examples (II-1) to (II-9). The reason is determined that introducing two nitrogen (N) atoms into a core (thienopyrimidine or furopyrimidine) having excellent hole characteristics allows an appropriate structural form to receive both holes and electrons, thereby easily achieving charge balance of holes and electrons, resulting in efficient emission of light in a light emitting layer. Further, it was confirmed that the resistance to electrons became strong, contributing to the improvement of the element life.
In addition, the characteristics of the element have been described in conjunction with the electron transport layer and the light emitting layer according to the evaluation results of the above-described element fabrication, but materials for the electron transport layer and the light emitting layer may be generally used alone or in a mixture with other materials for the aforementioned organic material layers for organic electronic elements, such as the electron injection layer, the hole transport layer, and the auxiliary light emitting layer. Therefore, for the above reasons, the compound of the present invention may be generally used alone or in a mixture with other materials for organic material layers other than the electron transport layer and the light emitting layer, such as an electron injection layer, a hole transport layer, and an auxiliary light emitting layer.
Although exemplary embodiments of the present invention have been described for illustrative purposes, those skilled in the art will appreciate that various modifications, additions and substitutions are possible, without departing from the scope and spirit of the invention as disclosed in the accompanying claims. Therefore, the disclosed embodiments of the present invention are intended to illustrate the scope of the technical idea of the present invention, and the scope of the present invention is not limited to the embodiments. The scope of the present invention should be construed based on the appended claims, and it should be understood that all technical ideas included in the scope equivalent to the claims belong to the present invention.
[ description of reference numerals ]
100: organic electronic component
110: substrate
120: a first electrode
130: hole injection layer
140: hole transport layer
141: buffer layer
150: luminescent layer
151: auxiliary luminescent layer
160: electron transport layer
170: electron injection layer
180: second electrode
Cross Reference to Related Applications
The present patent application claims priority from korean patent application No.10-2014-0064696, filed 2014, 5, 28, based on 35u.s.c. § 119(a), the disclosure of which is incorporated herein by reference. Further, the present patent application claims priority in countries other than the united states, with the same reason based on korean patent application, the entire contents of which are incorporated herein by reference.

Claims (9)

1. A compound represented by formula 2 or 3,
Figure FDA0002464167530000011
wherein, in the formulae 2 and 3,
m is an integer of 2 to 4;
R1r combined with each other to form at least one benzene ring without forming a benzene ring1Is hydrogen;
x is O or S;
Ar1and Ar2Each independently selected from C6-C30Aryl and C containing at least one heteroatom selected from O, N, S, Si and P2-C30Heterocyclic group;
L1and L2Each independently selected from the group consisting of a single bond and C6-C30Arylene group of the formula 2, L1And L2At least one of which is an arylene group; and
Ar1and Ar2Each of the aryl group and the heterocyclic group of (a) may be substituted with at least one substituent selected from the group consisting of: c6-C20Aryl and C2-C20A heterocyclic group.
2. The compound according to claim 1, wherein Ar in the above formulas 2 and 31And Ar2Each independently represented by one of formulae a1 to A8:
Figure FDA0002464167530000021
wherein in formulae A1 to A8,
n is an integer of 0 to 4; o is an integer from 0 to 5;
p is an integer from 0 to 6; r is an integer of 0 to 8;
Q1to Q11Each independently is CRcOr N;
Q12to Q15Each independently is C, CRdOr N;
w is S, O, NReOr CRfRg；
R2Is selected from C6-C20Aryl and C containing at least one heteroatom selected from O, N, S, Si and P2-C20A heterocyclic group, wherein when n, o, p and R are each an integer of 2 or more, a plurality of R2May be the same as or different from each other;
Rcand RdEach independently selected from hydrogen, C6-C20Aryl and C containing at least one heteroatom selected from O, N, S, Si and P2-C20Heterocyclic group;
Reto RgEach independently selected from C6-C20Aryl and C containing at least one heteroatom selected from O, N, S, Si and P2-C20Heterocyclic group; and
symbol represents and L1Or L2The connection of (2).
3. The compound of claim 1, wherein the compound is one of the following:
Figure FDA0002464167530000031
4. an organic electronic component comprising:
a first electrode;
a second electrode; and
an organic material layer disposed between the first electrode and the second electrode, wherein the organic material layer comprises the compound of any one of claims 1 to 3.
5. The organic electronic element according to claim 4, wherein the organic material layer comprises a light-emitting layer and an electron-transporting layer, and the compound is contained in at least one of the light-emitting layer and the electron-transporting layer alone or as a mixture.
6. The organic electronic element according to claim 4, further comprising a light efficiency improving layer formed on at least one face opposite to the organic material layer in one of one surface of the first electrode and the second electrode layer.
7. The organic electronic element according to claim 4, wherein the organic material layer is formed by a spin coating process, a nozzle printing process, an inkjet printing process, a slit coating process, a dip coating process, or a roll-to-roll process.
8. An electronic device, comprising:
a display device comprising the organic electronic element according to claim 4; and
a controller for driving the display device.
9. The electronic device according to claim 8, wherein the organic electronic element is one of an organic electronic light-emitting element, an organic solar cell, an organic photoconductor, an organic transistor, and an element for monochromatic or white illumination.
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